Acetic Acid → HCID 21524245, compound

HRID 917919Notes

Reaction equation

HRID 917919 reaction equation
C(C1[C:12]2[C:7](=[CH:8][C:9]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)=[C:10]([Cl:13])[CH:11]=2)[C:6](=[O:20])[CH2:5][CH2:4]1)#N.[C:21]([OH:24])(=[O:23])[CH3:22].S(=O)(=O)(O)O>O>[O:20]=[C:6]1[C:7]2[C:12](=[CH:11][C:10]([Cl:13])=[C:9]([CH:14]3[CH2:19][CH2:18][CH2:17][CH2:16][CH2:15]3)[CH:8]=2)[CH:22]([C:21]([OH:24])=[O:23])[CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 1118Sulfuric AcidHCID 21524239HCID 21524239, compound

Product 1

HCID 21524245HCID 21524245, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A mixture of 19 g of 4-cyano-6-chloro-7-cyclohexyl-3,4-dihydro-naphthalene-1(2H)-one, 36 ml of glacial acetic acid, 43 ml of concentrated sulfuric acid, and 29 ml of water is refluxed overnight. It is then poured into water, and the aqueous mixture is extracted with ethyl acetate. After drying and evaporation of the solvent, the residue is crystallized from toluene. There are obtained 14.3 g of 4-oxo-6-cyclohexyl-7-chloro-1,2,3,4-tetrahydro-naphthalene-1 -carboxylic acid melting at 204°-205°C, which product is identical with the compound of Example 3.

Workup

  1. temperatureis refluxed overnight
  2. extractionthe aqueous mixture is extracted with ethyl acetate
  3. customAfter drying
  4. customevaporation of the solvent
  5. customthe residue is crystallized from toluene

Sources & evidence

ORD record
ord-0864df298431421f9135355a67fb12b7
Source dataset
uspto-grants-1976_07
Patent number
US03968142

Reaction notes

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